Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae

The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAla-DVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla -LDab-DDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported.